Dyes of the benzene-naphthalene series and process their manufacture.



' end HEINREIKEZ Gllbii'llHfiGEN, OF BEBLIN HARLSHORST, K'I-ERIEU-LNY, ASSIEG'NDR TU JCMTTIEN GESELLSGHAFT ANILIN FABRHMTIUN, 01? BERLIN,

EYES 6313 THE BEliIZENE-NAiPHTHALENE SERIES AND PROCESS FOR THEIR MATJTU" Patented Fell FACTUBE.

31 255 $34M}; Specification of Letters Patent. ifo Drawing.

EILLD Now my present application is cover and claim new dyes of the benzene-naphthalene acridin series as represented by the general graphic formula:

in which formula R anti R mean univai "Fi l These N-dialkylatedbenzencmaplithalene acridin dyes may also be obtained by my new process in the reversed form, in heatbetanaphthylamm or by heating a lformyl Application filed July 29, 1916. Serial No. 112,198.

lent subsliitnenis, and more csg iecinlly an H atom or on allzyl group.

As typical examples of these new dyes the two following may be given:

ing, for instance, a formyl-derivetive of ii meta-am1no-d1methylan1l1n with a sale a,

. and 20.9

derivative of a el-amino-Z:dialliylaminotolw'uene with a salt ofa beta-naphthylamin.

we L1 The following examples serve to illustrate my invention, t e parts being by weight:

(1). 17.1 parts of formyl-Z-naphthylamin parts of 3-aminodimethylanilin- .hydrochlorid are melted together in an enameled iron vessel provided with an agitator and an oil bath; the temperature is gradually raised to ISO-190 C. The reaction is finished if the evolution of water vapors has ceased. The melt is then dissolved in boiling water, the solution filtered while hot and the dye precipitated from the filtrate by adding a solution of common salt and of zinc-chlorid.

The new dye thus obtained forms a brown red powder; it dyes leather clear and deep oran e tints.

2?. According to the indications given in Example l one melts together 17.1parts of formyl-Q-naphthylamin and 21 parts of 4- amino-2-methylaminototuene hydrochlorid.

The melt may be workedeup as given above; the new dye thus obtained forms in the dry state and pulverized a red brown powder dyeing leather clear and deep orange yellow tints.

(3). 17.1 parts of formyl-2-naphthylamin and 22.5 parts of 4-amino-2-dimethylaminotoluene -'hydrochlorid are melted together raisin the temperature gradually to 180 to 190 The new dye is separated from the melt according to the indications given The new process is then represented by the two equations:

methylaminotoluene and 17 .9 parts of betanaphthylarnin-hydrochlorid are melted together at about 170-190 C.; as to the gen eral conditions of reaction compare above. In working up the melt it may be preferable to add some hydrochloric aci i. The dye thus obtained is essentially the same as the product obtained according to Example 3.

My present invention is not limited to the foregoing examples or to the details and special conditions of reaction given therein. Thus for instance instead of beta-naphthyL amin itself a suitable chloroor hromoderivative thereof ma be used. Other suitable '65 salts than the hy rochlorids, for instance sulfates, may be employed. I

Having now described my invention what I claim is 1. As a new process for themanufacture of new dyes of the acridin series the process which consists in heating a formyl derivative of a beta-naphthylamin with a salt of a meta-diamin of the benzene series.

2. As a new process for the manufacture of new dyes of the acridin series the process which consists in heating a forniyl derivative of a beta-naphthylamin. with a salt of an alkylated meta-diamin of thebenzene series. V

3. As anew process for the manufacture of new dyes of the aeridin series the process which consists in heating a formyl derivative of a'beta-naphthylamin with a sale of an N-alkylated meta-diamin of the benzene series.

4;. As a new process for the manufacture of new dyes of the acridin series the process which consists in heating a formyl derivative of a beta-naphth'ylamin with a salt of a O- and N-alkylated meta-cliamin of the benzene series.

5. As a new process for the manufacture of a new dye of the acridin series the process which consists in heating formyl-betanaphthylamin with a salt of a meta-amino dimethyl derivative of a monamin of the benzene series.

ageee'mo' a 6. As a new process for the manufacture. of a new dye oi the acridin series the process which consists in heating formyl-betanaphthylamin with 4 ainino 2 dimethyi- 5 amino toluene-hy'drochlorid.

7. As new articles of msvwfactu e new dyes of the acridin series we general graphic formula 1 spoilds to the formula:

lent substituents.

'8. As a new article of manufacture the underlying 0t 'WillCil correnew dye of the acridin series corresponding to the formula: 2e

' rown N /Vx CLL/L which dye in the dry state and pulverized forqns a red brown powder dyeing leather clear and deep orange yellow tints' In testimony whereof I have aiiixed my signature in presence of two witnesses,

HEINRICH GRUNHAGEN. Witnesses HENRY HASPER,

ALLEN F. JENNINGS. 

